The Sox could pare down the payroll significantly each of the next two seasons without dumping Sale. You think his value is highest now, what if he puts up CY award seasons the next two years(including this one), his trade value would be through the roof. He'd still have three years at 9 mil/yr with two option years left. I'd rather the Sox hold on to him, if it looks hopeless in three years, then trade him. Giving up young ace pitchers doesn't usually turn out well, it's not like they're just growing on trees.

I don't think a Cy Young is going to change his value much, I think teams view him as one of the best pitchers in the game period. The problem is the health risk, and yeah a lot of people here don't think he'll get injured but if you're not competing in the meantime, why risk it? His value could go from marque to zilch overnight.